ELLEANE

Ethinylestradiol was first synthesized in by Hans Herloff Inhoffen and Walter Hohlweg at Schering.

It was developed in an effort to create an estrogen with greater oral bioavailability.

These properties were achieved by the substitution of an ethinyl group at carbon of estradiol.

Ethinylestradiol soon replaced mestranol in contraceptive pills.

Ethinylestradiol was granted

FDA approval on 25 June 1943.

Ethinylestradiol is combined with other drugs for use as a contraceptive, premenstrual dysphoric disorder, moderate acne, moderate to severe vasomotor symptoms of menopause, prevention of postmenopausal osteoporosis. 15, 25, 16, 17, 24, 18, 19, 20, 21, 22,

Ethinylestradiol is a synthetic estrogen that decreases luteinizing hormone to decrease endometrial vascularization, and decreases gonadotrophic hormone to prevent ovulation. 13, 12, 15 It has a long duration of action as it is taken once daily, and a wide therapeutic index as overdoses are generally not associated with serious adverse effects.

Patients should be counselled regarding the risks of thrombotic events.

A 30 µg oral dose of ethinylestradiol reaches a C max of 74.1±35.6pg/mL, with a T max of 1.5±0.5h, and an AUC of 487.4±166.6pg*h/mL.

A 1.2 mg dose delivered via a patch reaches a C max of 28.8±10.3pg/mL, with a T max of 86±31h, and an AUC of3895±1423pg*h/mL.

A 30 µg oral dose has an apparent volume of distribution of 625.3±228.7 L and a 1.2 mg topical dose has an apparent volume of distribution of 11745.3±15934.8 L.

Ethinylestradiol can be glucuronidated by

UGT1A1, UGT1A3, UGT1A4, UGT1A9, and UGT2B7. 3, 7 Ethinylestradiol is also sulfated by SULT1A1, SULT1A3, and SULT1E1. 6, 7 Ethinylestradiol can also be hydroxylated at positions 2, 4, 6, 7, and 16 5, 7 by CYP3A4, CYP3A5, CYP2C8, CYP2C9, and CYP1A2. 4, 7 These hydroxylated metabolites can be methylated by catechol-O-methyltransferase.

The methoxy metabolites can in turn be sulfated or glucuronidated.

Hover over products below to view reaction partners Ethinylestradiol Ethinylestradiol-3-sulfate Ethinylestradiol-glucuronide 2-hydroxyethinylestradiol 2-methoxyethinylestradiol 4-hydroxyethinylestradiol 4-methoxyethinylestradiol 6-hydroxyethinylestradiol 6-methoxyethinylestradiol 7-hydroxyethinylestradiol 7-methoxyethinylestradiol 16α-hydroxyethinylestradiol 16α-methoxyethinylestradiol.

Ethinylestradiol is 59.2% eliminated in the urine and bile, while 2-3% is eliminated in the feces.

Over 90% of ethinylestradiol is eliminated as the unchanged parent drug.

A 30 µg oral dose has a half life of 8.4±4.8h and a 1.2 mg topical dose has a half life of 27.7±34.2h.

Ethinylestradiol has an intravenous clearance of 16.47 L/h, and an estimated renal clearance of approximately 2.1 L/h.

A 30 µg oral dose has a clearance of 58.0±19.8 L/h and a 1.2 mg topical dose has a clearance of 303.5±100.5 L/h.

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Female patients experiencing and overdose may present with withdrawal bleeding, nausea, vomiting, breast tenderness, abdominal pain, drowsiness, and fatigue. 15, 25, 16, 17, 24, 18, 19, 20, 21, 22, 23 Overdose should be treated with symptomatic and supportive care including monitoring for potassium concentrations, sodium concentrations, and signs of metabolic acidosis. 15, 25, 16, 17, 24, 18, 19, 20, 21, 22, 23.